Conversation Turned Awkward

So I have this friend...
Ever start a conversation this way? It just seems so awkward to me. Sometimes when people start out that way they're really talking about themselves. Other times they really mean that they have this friend that something happened to. No matter how you really meant it to be it always seems to turn into a fail. The way I see it there's four possible ways it could go. You could tell the story and the person you're telling could be like "When you say a friend, do you mean you?" which could end in either, "No, I really mean a friend." or the awkward "yeah". Then there's you telling the story and the person doesn't get that you're trying to hint that it really is about you. Finally you could tell the story and the other person doesn't question it. So you have a 1/4 chance to avoid the awkward moment that came out of trying to make conversation.
~Lauren